NO120685B - - Google Patents

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Info

Publication number: NO120685B
Authority: NO; Norway
Prior art keywords: formula; symbols; compounds; ethers; activity
Prior art date: 1966-09-16

Application number

NO16975567A

Other languages

English (en)

Norwegian (no)

Inventor

W Nauta

Original Assignee

Koninklijke Pharma Fab Nv

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1966-09-16

Filing date

1967-09-15

Publication date

1970-11-23

1967-09-15 Application filed by Koninklijke Pharma Fab Nv filed Critical Koninklijke Pharma Fab Nv

1970-11-23 Publication of NO120685B publication Critical patent/NO120685B/no

Links

150000001875 compounds Chemical class 0.000 claims description 26
-1 benzhydrylaminopropanol ethers Chemical class 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 2
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
230000000694 effects Effects 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
206010003119 arrhythmia Diseases 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
230000006793 arrhythmia Effects 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
GJHKWLSRHNWTAN-UHFFFAOYSA-N 1-ethoxy-4-(4-pentylcyclohexyl)benzene Chemical compound C1CC(CCCCC)CCC1C1=CC=C(OCC)C=C1 GJHKWLSRHNWTAN-UHFFFAOYSA-N 0.000 description 4
XFSBVAOIAHNAPC-XTHSEXKGSA-N 16-Ethyl-1alpha,6alpha,19beta-trimethoxy-4-(methoxymethyl)-aconitane-3alpha,8,10alpha,11,18alpha-pentol, 8-acetate 10-benzoate Chemical compound O([C@H]1[C@]2(O)C[C@H]3[C@@]45C6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)[C@@H]4[C@]([C@@H](C[C@@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-XTHSEXKGSA-N 0.000 description 4
XFSBVAOIAHNAPC-UHFFFAOYSA-N Aconitin Natural products CCN1CC(C(CC2OC)O)(COC)C3C(OC)C(C(C45)(OC(C)=O)C(O)C6OC)C1C32C4CC6(O)C5OC(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-UHFFFAOYSA-N 0.000 description 4
CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 4
229940039750 aconitine Drugs 0.000 description 4
STDXGNLCJACLFY-UHFFFAOYSA-N aconitine Natural products CCN1CC2(COC)C(O)CC(O)C34C5CC6(O)C(OC)C(O)C(OC(=O)C)(C5C6OC(=O)c7ccccc7)C(C(OC)C23)C14 STDXGNLCJACLFY-UHFFFAOYSA-N 0.000 description 4
LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 4
229960004482 quinidine sulfate Drugs 0.000 description 4
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
AMFIUYBZYJZWAU-UHFFFAOYSA-N 2-(benzhydryloxymethyl)oxirane Chemical compound C1OC1COC(C=1C=CC=CC=1)C1=CC=CC=C1 AMFIUYBZYJZWAU-UHFFFAOYSA-N 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
230000003288 anthiarrhythmic effect Effects 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
229960001317 isoprenaline Drugs 0.000 description 3
239000001294 propane Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
UEISDADHNFFLJH-UHFFFAOYSA-N C(O)(NC(C1=CC=CC=C1)C1=CC=CC=C1)CC Chemical compound C(O)(NC(C1=CC=CC=C1)C1=CC=CC=C1)CC UEISDADHNFFLJH-UHFFFAOYSA-N 0.000 description 2
241000700199 Cavia porcellus Species 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
208000006218 bradycardia Diseases 0.000 description 2
230000036471 bradycardia Effects 0.000 description 2
239000000812 cholinergic antagonist Substances 0.000 description 2
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
229960001404 quinidine Drugs 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
CNLSIIKAVMAJNX-UHFFFAOYSA-N 2-[bis(2,6-dimethylphenyl)methoxy]-n,n-dimethylethanamine;hydrochloride Chemical compound [Cl-].CC=1C=CC=C(C)C=1C(OCC[NH+](C)C)C1=C(C)C=CC=C1C CNLSIIKAVMAJNX-UHFFFAOYSA-N 0.000 description 1
FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
208000020446 Cardiac disease Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
208000007101 Muscle Cramp Diseases 0.000 description 1
208000005392 Spasm Diseases 0.000 description 1
239000000219 Sympatholytic Substances 0.000 description 1
ZDVDCDLBOLSVGM-UHFFFAOYSA-N [chloro(phenyl)methyl]benzene Chemical class C=1C=CC=CC=1C(Cl)C1=CC=CC=C1 ZDVDCDLBOLSVGM-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical group 0.000 description 1
238000010171 animal model Methods 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
229910001626 barium chloride Inorganic materials 0.000 description 1
239000002585 base Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000008602 contraction Effects 0.000 description 1
210000004351 coronary vessel Anatomy 0.000 description 1
230000001186 cumulative effect Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical class C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000006735 epoxidation reaction Methods 0.000 description 1
XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
AKPUJVVHYUHGKY-UHFFFAOYSA-N hydron;propan-2-ol;chloride Chemical compound Cl.CC(C)O AKPUJVVHYUHGKY-UHFFFAOYSA-N 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
230000001788 irregular Effects 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
NZWOPGCLSHLLPA-UHFFFAOYSA-N methacholine Chemical compound C[N+](C)(C)CC(C)OC(C)=O NZWOPGCLSHLLPA-UHFFFAOYSA-N 0.000 description 1
229960002329 methacholine Drugs 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
229960003343 ouabain Drugs 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
229960001789 papaverine Drugs 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000006187 phenyl benzyl group Chemical group 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000000948 sympatholitic effect Effects 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000004448 titration Methods 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO16975567A 1966-09-16 1967-09-15 NO120685B (da)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB4154166A GB1170274A (en)	1966-09-16	1966-09-16	Benzhydryl or Dibenzocycloheptenyl Aminopropanol Ethers

Publications (1)

Publication Number	Publication Date
NO120685B true NO120685B (da)	1970-11-23

Family

ID=10420177

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO16975567A NO120685B (da)	1966-09-16	1967-09-15

Country Status (13)

Country	Link
BE (1)	BE703942A (da)
CA (1)	CA964654A (da)
CH (1)	CH522591A (da)
CS (1)	CS166221B2 (da)
DE (1)	DE1668493C3 (da)
DK (1)	DK118465B (da)
ES (1)	ES345088A1 (da)
FR (2)	FR1558326A (da)
GB (1)	GB1170274A (da)
IL (1)	IL28628A (da)
NL (1)	NL148042B (da)
NO (1)	NO120685B (da)
SE (1)	SE338781B (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2333501A2 (fr)	1975-12-03	1977-07-01	Science Union & Cie	Nouveaux acetamides substitues leurs procedes d'obtention et les compositions pharmaceutiques en renfermant

1966
- 1966-09-16 GB GB4154166A patent/GB1170274A/en not_active Expired
1967
- 1967-09-12 IL IL2862867A patent/IL28628A/en unknown
- 1967-09-13 SE SE1263367A patent/SE338781B/xx unknown
- 1967-09-15 ES ES345088A patent/ES345088A1/es not_active Expired
- 1967-09-15 FR FR1558326D patent/FR1558326A/fr not_active Expired
- 1967-09-15 BE BE703942D patent/BE703942A/xx unknown
- 1967-09-15 DE DE19671668493 patent/DE1668493C3/de not_active Expired
- 1967-09-15 DK DK462967A patent/DK118465B/da unknown
- 1967-09-15 CA CA000,182A patent/CA964654A/en not_active Expired
- 1967-09-15 CH CH1291467A patent/CH522591A/de not_active IP Right Cessation
- 1967-09-15 NO NO16975567A patent/NO120685B/no unknown
- 1967-09-18 NL NL6712697A patent/NL148042B/xx unknown
- 1967-09-18 CS CS663467A patent/CS166221B2/cs unknown
- 1967-12-13 FR FR132004A patent/FR8370M/fr not_active Expired

Also Published As

Publication number	Publication date
CA964654A (en)	1975-03-18
NL148042B (nl)	1975-12-15
DE1668493C3 (de)	1974-04-18
IL28628A (en)	1971-10-20
GB1170274A (en)	1969-11-12
DK118465B (da)	1970-08-24
SE338781B (da)	1971-09-20
CH522591A (de)	1972-06-30
ES345088A1 (es)	1969-01-16
BE703942A (da)	1968-03-15
CS166221B2 (da)	1976-02-27
DE1668493A1 (de)	1971-06-09
FR1558326A (da)	1969-02-28
FR8370M (da)	1971-02-22
NL6712697A (da)	1968-03-18
DE1668493B2 (de)	1973-09-13

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